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Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

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journal contribution
posted on 19.03.2009, 00:00 by Lawrence L. W. Cheung, Andrei K. Yudin
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing δ-lactams can be accessed from N-vinyl-β-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane δ-lactams in a diastereoselective manner.

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